People have been traveling from Badwater (279' below sea level) to Mt Whitney (14,505') by various means for decades (https://en.wikipedia.org/wiki/Badwater_Ultramarathon).  The most standard route is about 135 miles of paved roads to Whitney Portal, followed by 11 miles up the Mt Whitney Trail, though some have used the shorter, harder Mountaineers Route.  The Badwater 135 is an annual (supported) event in July covering just the road part, though competitors sometim

Joseph Nuara submitted the route:

The Woodbridge Greenway loop is a combination of several blue-blazed trail systems spanning through the towns of Hamden, Woodbridge, and New Haven in Connecticut. The 23mi course starts and finishes at West Rock State Park at the Lake Wintergreen parking lot and traverses through several of the Woodbridge Greenway trails, Yale Nature Preserve, the Maltby Lakes, and a short section through the sub-town of Westville before returning to the southern tip of West Rock State Park and returning to the start.